title: Palladium-catalyzed oxidative acetoxylation of benzylic C-H bond using bidentate auxiliary.
abstract: Pd(OAc)2-catalyzed oxidative acetoxylation of benzylic C-H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI(OAc)2 in the presence of Pd(OAc)2 to afford the acetoxylated products in synthetically useful yields. A broad of functionalities, such as CH3, F, Cl, Br, I, COCH3, CO2Et, SO2CH3, and NO2, were tolerated. This transformation provides easy access to 2-hydroxymethylaniline derivatives.
authors.affiliation: ZJU-NHU United R&D Center, Department of Chemistry, Zhejiang University , Hangzhou 310027, China.
authors.forename: Long
authors.initials: L
authors.lastname: Ju
authors.forename: Jinzhong
authors.initials: J
authors.lastname: Yao
authors.forename: Zaihong
authors.initials: Z
authors.lastname: Wu
authors.forename: Zhanxiang
authors.initials: Z
authors.lastname: Liu
authors.forename: Yuhong
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*
chemical_list: C000588726:2-hydroxymethylaniline; D000814:Aniline Compounds; D001593:Benzyl Compounds; D010165:Palladium